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Winter Haven is located in Central Florida and known for its canal-linked Chain of Lakes. Several lakes have waterside parks and eateries, as well as boat ramps and water-sports rentals. On Lake Eloise, Legoland Florida Resort includes Cypress Gardens, a 1930s botanical garden, and Lego-brick attractions, rides and a water park. West of the city, Circle B Bar Reserve has forest trails and alligator-inhabited wetlands. Use our custom search tool to view all pool homes for sale under $400k in Winter Haven or click here to return to the list of surrounding towns and cities in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 808 Lake Elbert Court, Winter Haven, FL 33881 (MLS # P4933235)
    $395,000
    Photo of 808 Lake Elbert Court, Winter Haven, FL 33881 (MLS # P4933235)
    Photo of 808 Lake Elbert Court, Winter Haven, FL 33881 (MLS # P4933235)
    808 Lake Elbert Court, Winter Haven, FL
    808 Lake Elbert Court
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,644 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  2. Photo of 1360 10th Court NE, Winter Haven, FL 33881 (MLS # W7871788)
    $289,000
    Photo of 1360 10th Court NE, Winter Haven, FL 33881 (MLS # W7871788)
    Photo of 1360 10th Court NE, Winter Haven, FL 33881 (MLS # W7871788)
    1360 10th Court NE, Winter Haven, FL
    1360 10th Court NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,519 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  3. Photo of 824 Lake Elbert Court, Winter Haven, FL 33881 (MLS # O6274086)
    $300,000
    Photo of 824 Lake Elbert Court, Winter Haven, FL 33881 (MLS # O6274086)
    Photo of 824 Lake Elbert Court, Winter Haven, FL 33881 (MLS # O6274086)
    824 Lake Elbert Court, Winter Haven, FL
    824 Lake Elbert Court
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 3,377 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  4. Photo of 2105 Normandy Heights Lane, Winter Haven, FL 33880 (MLS # L4950189)
    $359,900
    Photo of 2105 Normandy Heights Lane, Winter Haven, FL 33880 (MLS # L4950189)
    Photo of 2105 Normandy Heights Lane, Winter Haven, FL 33880 (MLS # L4950189)
    2105 Normandy Heights Lane, Winter Haven, FL
    2105 Normandy Heights Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,843 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  5. Photo of 1776 6th Street NW #407, Winter Haven, FL 33881 (MLS # P4933409)
    $155,000
    Photo of 1776 6th Street NW #407, Winter Haven, FL 33881 (MLS # P4933409)
    Photo of 1776 6th Street NW #407, Winter Haven, FL 33881 (MLS # P4933409)
    1776 6th Street NW #407, Winter Haven, FL
    1776 6th Street NW #407
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,347 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  6. Photo of 156 Whitman Road, Winter Haven, FL 33884 (MLS # TB8340650)
    $315,000
    Photo of 156 Whitman Road, Winter Haven, FL 33884 (MLS # TB8340650)
    Photo of 156 Whitman Road, Winter Haven, FL 33884 (MLS # TB8340650)
    156 Whitman Road, Winter Haven, FL
    156 Whitman Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,609 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  7. Photo of 1700 6th Street NW #C27, Winter Haven, FL 33881 (MLS # L4950015)
    $84,900
    Photo of 1700 6th Street NW #C27, Winter Haven, FL 33881 (MLS # L4950015)
    Photo of 1700 6th Street NW #C27, Winter Haven, FL 33881 (MLS # L4950015)
    1700 6th Street NW #C27, Winter Haven, FL
    1700 6th Street NW #C27
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 640 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  8. Photo of 3648 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4950097)
    $280,000
    Photo of 3648 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4950097)
    Photo of 3648 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4950097)
    3648 Julius Estates Boulevard, Winter Haven, FL
    3648 Julius Estates Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,751 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  9. Photo of 2062 Katie Court, Winter Haven, FL 33884 (MLS # B4901808)
    $389,000
    Photo of 2062 Katie Court, Winter Haven, FL 33884 (MLS # B4901808)
    Photo of 2062 Katie Court, Winter Haven, FL 33884 (MLS # B4901808)
    2062 Katie Court, Winter Haven, FL
    2062 Katie Court
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,664 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  10. Photo of 2488 Hartridge Point Drive W #2488, Winter Haven, FL 33881 (MLS # A4635538)
    $229,900
    Photo of 2488 Hartridge Point Drive W #2488, Winter Haven, FL 33881 (MLS # A4635538)
    Photo of 2488 Hartridge Point Drive W #2488, Winter Haven, FL 33881 (MLS # A4635538)
    2488 Hartridge Point Drive W #2488, Winter Haven, FL
    2488 Hartridge Point Drive W #2488
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,188 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  11. Photo of 1592 Martin Luther King Boulevard NE, Winter Haven, FL 33881 (MLS # S5118159)
    $315,000
    Photo of 1592 Martin Luther King Boulevard NE, Winter Haven, FL 33881 (MLS # S5118159)
    Photo of 1592 Martin Luther King Boulevard NE, Winter Haven, FL 33881 (MLS # S5118159)
    1592 Martin Luther King Boulevard NE, Winter Haven, FL
    1592 Martin Luther King Boulevard NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 21,780 Lot (sqft)
  12. Photo of 1001 Mockingbird Circle, Winter Haven, FL 33884 (MLS # P4933140)
    $350,000
    Photo of 1001 Mockingbird Circle, Winter Haven, FL 33884 (MLS # P4933140)
    Photo of 1001 Mockingbird Circle, Winter Haven, FL 33884 (MLS # P4933140)
    1001 Mockingbird Circle, Winter Haven, FL
    1001 Mockingbird Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,853 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  13. Photo of 5850 Cypress Gardens Boulevard #304, Winter Haven, FL 33884 (MLS # O6266648)
    $184,947
    Photo of 5850 Cypress Gardens Boulevard #304, Winter Haven, FL 33884 (MLS # O6266648)
    Photo of 5850 Cypress Gardens Boulevard #304, Winter Haven, FL 33884 (MLS # O6266648)
    5850 Cypress Gardens Boulevard #304, Winter Haven, FL
    5850 Cypress Gardens Boulevard #304
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,332 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  14. Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    $399,500
    Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    218 College Grove Circle NE, Winter Haven, FL
    218 College Grove Circle NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,109 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  15. Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    $319,800
    Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    2521 Avenue A SW, Winter Haven, FL
    2521 Avenue A SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,075 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  16. Photo of 723 Canberra Road, Winter Haven, FL 33884 (MLS # P4933004)
    $349,900
    Photo of 723 Canberra Road, Winter Haven, FL 33884 (MLS # P4933004)
    Photo of 723 Canberra Road, Winter Haven, FL 33884 (MLS # P4933004)
    723 Canberra Road, Winter Haven, FL
    723 Canberra Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,006 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  17. Photo of 1610 Meadow Lane NE, Winter Haven, FL 33881 (MLS # P4932958)
    $359,900
    Photo of 1610 Meadow Lane NE, Winter Haven, FL 33881 (MLS # P4932958)
    Photo of 1610 Meadow Lane NE, Winter Haven, FL 33881 (MLS # P4932958)
    1610 Meadow Lane NE, Winter Haven, FL
    1610 Meadow Lane NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,672 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  18. Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    $314,900
    Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    3136 Country Club Circle, Winter Haven, FL
    3136 Country Club Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  19. Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    $224,000
    Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    1392 Innsbruck Ct, Winter Haven, FL
    1392 Innsbruck Ct
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,369 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  20. Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    $277,000
    Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    1956 28th Street NW, Winter Haven, FL
    1956 28th Street NW
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 1,974 Home (sqft)
    • 1 Bath
    • 7,841 Lot (sqft)
  21. Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    $254,000
    Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    1644 Linz Ct, Winter Haven, FL
    1644 Linz Ct
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,329 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  22. Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    $269,000
    Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    217 W Lake Ina Drive, Winter Haven, FL
    217 W Lake Ina Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,360 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  23. Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    $385,000
    Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    220 Escambia Drive, Winter Haven, FL
    220 Escambia Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,701 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  24. Photo of 6019 Live Oak Drive, Winter Haven, FL 33880 (MLS # O6256194)
    $365,000
    Photo of 6019 Live Oak Drive, Winter Haven, FL 33880 (MLS # O6256194)
    Photo of 6019 Live Oak Drive, Winter Haven, FL 33880 (MLS # O6256194)
    6019 Live Oak Drive, Winter Haven, FL
    6019 Live Oak Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,058 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  25. Photo of 2117 High Point Avenue SW, Winter Haven, FL 33880 (MLS # TB8317602)
    $300,000
    Photo of 2117 High Point Avenue SW, Winter Haven, FL 33880 (MLS # TB8317602)
    Photo of 2117 High Point Avenue SW, Winter Haven, FL 33880 (MLS # TB8317602)
    2117 High Point Avenue SW, Winter Haven, FL
    2117 High Point Avenue SW
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,485 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  26. Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    $250,000
    Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    307 La Serena, Winter Haven, FL
    307 La Serena
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,389 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  27. Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    $249,900
    Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    104 Brad Circle, Winter Haven, FL
    104 Brad Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,370 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  28. Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    $333,000
    Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    645 Augusta Road, Winter Haven, FL
    645 Augusta Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,140 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  29. Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    $355,000
    Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    3027 Buckeye Pointe Drive, Winter Haven, FL
    3027 Buckeye Pointe Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,132 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  30. Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    $270,000
    Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    728 Waterbridge Drive, Winter Haven, FL
    728 Waterbridge Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,320 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 1/27/25 4:30 PM PST.

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